Sodium Carbonate → 5-(4-Methoxyphenyl)-3-(1-methylpiperidin-4-yl)-1-(triisopropylsilyl)-indole

Participants

Reaction Steps

The title compound was prepared by the procedure of Example 10, beginning with 5-bromo-3-(1-methylpiperidin-4-yl)-1-(triisopropylsilyl)-indole (0.600 g, 1.34 mmol), 4-methoxyphenylboronic acid (0.213g, 1.40 mmol), tetrakis(triphenylphosphine)palladium(0) (0.077g, 0.067 mmol), and 2M aqueous sodium carbonate solution (2 mL) in toluene (15 mL) to give 0.150 g of 5-(4-methoxyphenyl)-3-(1-methylpiperidin-4-yl)-1-(triisopropylsilyl)-indole (24%) as a solid, which was desilylated by dissolving in 1 mL of tetrahydrofuran and treating with tetrabutylammonium fluoride (1M in tetrahydrofuran, 4 mL) to give the title compound (0.050 g, 45%) as an amorphous solid. FDMS m/e 320 (M+). EA calculated for C21H24N2O.⅛ H2O: C, 78.17; H, 7.57; N, 8.68. Found: C, 78.13; H, 7.92; H, 8.43.

Provenance & Evidence